Colbie Caillat

The "Bubbly" singer records her breakthrough album

Breakthrough, the title of Colbie Caillat's sophomore release (set for August), could just as aptly describe her 2007 debut, Coco, which featured the fresh-faced singer's smash hit "Bubbly," went platinum, and garnered attention from the likes of John Mayer (who invited her on his 2008 summer tour) and Taylor Swift (with whom she cowrote "Breathe"). We caught up with Caillat to chat about the new record, pulling pranks on Mayer, and the benefits of dating friends.

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Tell me about Breakthrough. I was going through a really rough time for a while—being in the spotlight was strange for me. I was always shy and had a huge fear of being onstage. I was contemplating quitting, but then I realized that I do want this and I was giving up too easily. I had to break through all my fears and insecurities and really try hard to become the person I want to be. And so I wanted to send that message out to people because I know we all feel like we're the only ones who have insecurities.

How is it a departure from Coco? It has the same vibe, but I think I've matured a lot over the past couple of years, and I've been working with different songwriters and had more life experiences. And I've been open to different instruments and production styles, so I think it's a little bit more grown-up and a little bit more sophisticated.

Are there any songs in particular that you think will take off the way "Bubbly" did? Well "Fallin' for You" is the first single, and it's about falling for a guy I was friends with. We went out on a date and I realized that there was no one else in the room. The room was silent, and I was on this high from it the next day and wrote this song.

Do you recommend dating friends? I do if it's after a long time and you know everything about that person—both their flaws and their good qualities—and you still like them. I think it makes for a much better relationship. I think it will last that much longer if it's someone that you care about inside and out instead of just a person you met on a date. That can go fine too, but I've found it works best for me the other way.

Andrew Southam

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Tell me about the video for "Fallin' for You." Bobby Moynihan from SNL plays my love interest, and the whole video is about this guy who's not my type, but he does all these dorky things on our date that somehow impress me. So he picks the roses from my garden instead of buying me flowers. And then we're going to go surfing and he almost hits me over the head with the surfboard. And he also has this really funny fantasy dream where he's dressed all "Guido" in white shoes and his chest is showing and I'm in this ridiculous bathing suit with huge hair and we're dancing at a DJ party on the beach. It's just a funny, silly video.

Your father, Ken Caillat, coproduced the seminal Fleetwood Mac albums Rumours and Tusk. Did you grow up hanging out with Stevie Nicks and John McVie? Yeah, I got to see all of them, but at the time I didn't know that Fleetwood Mac was such a big deal because I was so young. Now looking back, I think it's the coolest thing ever, but at the time, they were just my parents' friends. We would go see their concerts and go out on their boat in Malibu and meet them in Hawaii and it was just a normal thing with family friends.

Who are your musical icons? Bob Marley is a huge influence. I love reggae music, but I also love the purpose of the songs he writes and the style of the music—it takes your worries away and makes you feel good, and I think that's what music is about. So when I write songs, I want them to make people feel that same way. Lauryn Hill is another. She's the one who inspired me to become a singer. I fell in love with her voice and have tried to sound like her my whole life. I love John Mayer as well.

What was it like touring with him? That was a dream come true. He was one of my idols, and I got to watch his performances and learn from how he does it. It was a great experience for me to see how I can make my shows better from watching him.

What was he like to work with? Did he pull any pranks on you, à la sneaking up on Sheryl Crow in the bear suit? We didn't do pranks like that, but at the end of our show at the end of our tour, he came out and surprised me and sang on "Realize," and the whole crowd went nuts! I was shaking because I couldn't believe that was happening. So then I surprised him and went out and sang "Gravity" with him at the end of his show.

What's been your favorite live performance?

Maybe performing on SNL with Jason Mraz. I grew up watching SNL, and I always was a fan of Jason Mraz, and then I became friends with him when we wrote a song. When we got a chance to perform it on SNL, it was just an unreal moment in my lifetime.